I talk to business owners every week who’ve been burned by a bad experience with an assistant. And honestly? The feelings go beyond disappointment. There’s real fear there. Fear of wasting more time, more money, more energy on something that’s just not going to work out.
I get it. And I want to paint you a different picture.
Because when I dig into what actually went wrong, it’s rarely that the person they hired was terrible. It’s that there was a mismatch between what they needed and what they got. And that mismatch can make or break the whole experience.
The real reason it didn’t work
Most people hire “an assistant” without getting clear on what level of support they actually need. And that’s where things start to go sideways.
There’s a big difference between a junior admin assistant who needs detailed instructions for basic tasks and an experienced executive assistant who can anticipate needs and take ownership. There’s also a difference between a generalist and a specialist with deep expertise in bookkeeping, social media, or systems. And then some fractional executives operate at a strategic level.
When you expect proactive, senior-level thinking and hire someone equipped for task execution, frustration is inevitable. It’s not that they’re bad at their job. It’s that the job you needed wasn’t the job they were hired to do.
What those experiences can teach you
If you’ve been burned before, you actually have valuable insight. Those frustrations are clues about what you need this time around.
If you found yourself constantly following up and reminding… You need someone who takes initiative. Someone who sees what needs to happen next without being told. Someone who can take something and run with it.
If things fell through the cracks or got done incorrectly… You may need someone with more experience or clearer systems and processes to support the work.
If communication felt like a struggle… Consider whether time zones, communication styles, or availability were the real culprits. Someone who works your hours and communicates the way you do makes a bigger difference than most people expect.
If you felt like you were managing more than delegating… You might need a higher level of support. Someone who can own outcomes, not just complete tasks. Someone you don’t have to keep repeating yourself to.
If content got posted without approval or things happened that shouldn’t have… That’s a trust and process issue. The right partner will establish clear check-ins and boundaries before taking action.
What to look for this time
The goal isn’t just to find help; it’s to find the right help. Someone whose skills, experience, and working style match what your business actually needs right now. That’s what will make it work.
1. Clarity on the level of support you need. Are you looking for someone to execute a defined task list, or someone who can help you figure out what should be on that list in the first place? Being honest about this upfront saves everyone time.
2. A focus on fit, not just skills. Technical ability matters, but so does communication style, personality, and how someone approaches problem-solving. The best working relationships feel like partnerships, not management projects.
3. Proactive, not reactive. Look for someone who asks good questions, flags potential issues, and brings ideas to the table. Not someone who waits to be told what to do.
4. Experience that matches your expectations. If you want senior-level judgment, make sure you’re hiring someone with the experience to back it up. Junior support can be wonderful for the right tasks, but it’s not a substitute for seasoned expertise.
5. A process for getting aligned. The best partnerships start with clarity. Before hours begin, there should be a real conversation about your goals, your challenges, and what success looks like. Skipping this step is often where things go wrong.
Delegation isn’t the problem. Fit is.
If past experiences have made you hesitant to try again, that’s understandable. But the answer isn’t to keep doing everything yourself. That path leads to burnout, bottlenecks, and a business that can’t grow beyond your personal capacity.
When the fit is right, delegation actually works. You get time back. You get mental space back. And you get to focus on the work only you can do.
That’s what success can look like. And it’s exciting for me to help people see that it’s possible.
At Trusty Oak, we spend more time than most making sure we find the right match. If you’re ready to try delegation again, book a discovery call. No pressure, just clarity.